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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-06-12 17:35:25 UTC
HMDB IDHMDB0000999
Secondary Accession Numbers
  • HMDB00999
Metabolite Identification
Common NamePhosphoribosylformylglycinamidine
DescriptionPhosphoribosylformylglycinamidine, also known as formylglycinamidine ribonucleotide (FGAM), is a substrate for glucosamine-6-phosphate isomerase. Phosphoribosylformylglycinamidine is found in many foods, some of which are greenthread tea, cardamom, mulberry, and carrot.
Structure
Data?1560360925
Synonyms
ValueSource
FGAMHMDB
Formylglycinamidine ribonucleotideHMDB
N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-beta-D-ribofuranosyl)-formamideHMDB
N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-beta-D-ribofuranosyl)formamideHMDB
N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-β-D-ribofuranosyl)-formamideHMDB
N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-β-D-ribofuranosyl)formamideHMDB
PhosphoribosylformylglycinamidineHMDB
PhosphoribosylformylglycineamidineHMDB
Chemical FormulaC8H16N3O8P
Average Molecular Weight313.203
Monoisotopic Molecular Weight313.067501485
IUPAC Name{[(2R,3S,4R,5R)-5-[N-(carbamimidoylmethyl)formamido]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-[N-(carbamimidoylmethyl)formamido]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number37721-04-3
SMILES
NC(=N)CN(C=O)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C8H16N3O8P/c9-5(10)1-11(3-12)8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H3,9,10)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1
InChI KeyWQXXBAWHDQWCKL-XVFCMESISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Tertiary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.65 g/LALOGPS
logP-2.5ALOGPS
logP-4.2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)11.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.63 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.84 m³·mol⁻¹ChemAxon
Polarizability26.53 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022360
KNApSAcK IDNot Available
Chemspider ID62986231
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131878633
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jayaram HN, Lui MS, Plowman J, Pillwein K, Reardon MA, Elliott WL, Weber G: Oncolytic activity and mechanism of action of a novel L-cysteine derivative, L-cysteine, ethyl ester, S-(N-methylcarbamate) monohydrochloride. Cancer Chemother Pharmacol. 1990;26(2):88-92. [PubMed:2347042 ]
  2. Maegawa T, Karasawa T, Ohta T, Wang X, Kato H, Hayashi H, Nakamura S: Linkage between toxin production and purine biosynthesis in Clostridium difficile. J Med Microbiol. 2002 Jan;51(1):34-41. [PubMed:11800470 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295
Reactions
Adenosine triphosphate + Phosphoribosylformylglycinamidine → ADP + Phosphate + 5-Aminoimidazole ribonucleotidedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PFAS
Uniprot ID:
O15067
Molecular weight:
144733.165
Reactions
Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycinamide + L-Glutamine + Water → ADP + Phosphate + Phosphoribosylformylglycinamidine + L-Glutamic aciddetails